At what age should kids get more freedom?

At what age should parents start giving more independence to their children?
It’s a serious question I’m posing, as the parent of a 5-year-old, because I don’t have a clue as to what the correct answer is.
My son, Braden, as an only child, has been constantly under the watchful eye of my wife, Jenny, me, both of us, or a grandparent, aunt or babysitter. We have never allowed him to play outside by himself, and we certainly wouldn’t let him wander off alone at places like stores we go to on a regular basis.
The option to play outside is only available when someone is available to watch him while he’s out there. Jenny and I try our best to oblige, because we know he’s a much better behaved boy when he’s worn out from playing; however, sometimes our schedules, household work and energy levels don’t allow us to do so.
He’s also restricted to following us at any stores we go to, and visiting the toy aisle only happens if one of us is in the mood to go there.
Often, I feel bad he’s prohibited from experiencing many of the freedoms I had as a kid.
I remember having free reign outside in our neighborhood. I went with the neighbor kids to the school on our block and played with the playground equipment. I rode my Hot Wheels tricycle around the block, and I came home with plenty of cuts and bruises from playing too hard.
The only true negative experience I can recall occurred when I had to walk home by myself once from preschool. My younger sister was really sick and my mother didn’t want to risk taking her outside to get me. I was told by my teachers I should walk the four blocks back to my home.
I probably wouldn’t have had a problem with it if it hadn’t been for the busy intersection I had to cross. Afraid of it, I stood on the corner and cried for 10 minutes until some kind gentleman stopped and asked what was wrong. When I told him I couldn’t cross the road – I know, it sounds like a bad “Why did the chicken cross the road” joke – he offered to take me home. I kindly took him up on his offer, and fortunately for me, he did take me safely home.
I also remember bolting from my mother’s side the minute we walked into a store for the toy aisle. There, I played with every toy I could get my hands on, even if it meant opening the packaging to get to it. Back then, toy packaging didn’t come with a level of security equal to the security at Fort Knox, so I was able to try nearly every toy before I ever got it. I’m convinced I’m probably the reason parents need a master’s degree in engineering now to get toys out of their packages.
I had freedom to do all of these things as a youngster because it was the late 1970s and early 1980s, a time when people didn’t fear kidnappers, molesters, murderers, gangs and drugs as much as we do now. Sure, all these bad things were definitely around then, probably as much as they are now, but they weren’t on people’s minds as often because the media, including the fictional television programs and films we watch, didn’t talk about them all the time.
It’s good they do, because these are legitimate concerns, but the focus on them has made us a much more cynical nation, and as a result my wife and I worry about allowing Braden to play outside by himself or visiting the toy aisle alone.
In fairness, we live in an apartment in a highly residential area in Plover, with quite a bit of traffic that we also fear, especially with the high amount of bad drivers on the road who might be too distracted talking on their cell phones to see a kid playing on his bike. We purchased land in a much quieter neighborhood where we plan on constructing a house within the next year. We already have plans to give him more freedom when we move there.
In the meantime, though, when can we allow him to look at toys by himself or do things without our presence? People with answers should e-mail me at countyfare@pcgazette.com, or post an answer at my blog site at scottsteucklightofday.blogspot.com. Your answers may be featured in an upcoming column.